5-氰基-2-萘甲酸甲酯 | 91804-23-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 5-氰基-2-萘甲酸甲酯
• 英文名称: 5-cyanonaphthalene-2-carboxylic acid methyl ester
• 英文别名: 5-Cyan-<2>naphthoesaeure-methylester；5-Cyan-naphthoesaeure-(2)-methylester；Methyl 5-cyanonaphthalene-2-carboxylate
• CAS: 91804-23-8
• 化学式: C₁₃H₉NO₂
• 分子量: 211.22
• InChiKey: DCWCNMSLTJKVOY-UHFFFAOYSA-N

物化性质

• 熔点：
  114.5-115.5 °C(Solv: ethanol (64-17-5))
• 沸点：
  379.4±15.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-氰基-2-萘甲酸甲酯 在 吡啶 、 sodium hydroxide 、 叠氮磷酸二苯酯 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 80.0h， 生成 4-[[[5-[(E)-2-[3-(trifluoromethyl)phenyl]vinyl]-2-naphthyl]amino]methyl]benzoic acid
  参考文献：
  名称：

  Design and Syntheses of 1,6-Naphthalene Derivatives as Selective HCMV Protease Inhibitors

  摘要：

  Through high throughput screening of various libraries, substituted styryl naphthalene 6 was identified as an HCMV protease inhibitor. Optimization of various regions of the lead molecule using parallel synthesis resulted in 1,6-substituted naphthalenes 19d-i. These compounds displayed good potency and were selective over elastase, trypsin, and chymotrypsin. The optimization approach on lead compound 6 in three different regions of the molecule using parallel solution-phase synthesis and the corresponding SAR are discussed in detail.

  DOI：

  10.1021/jm030540h
• 作为产物：
  描述：

  5-溴-2-萘甲酸 在 吡啶 、 盐酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 5-氰基-2-萘甲酸甲酯
  参考文献：
  名称：

  Design and Syntheses of 1,6-Naphthalene Derivatives as Selective HCMV Protease Inhibitors

  摘要：

  Through high throughput screening of various libraries, substituted styryl naphthalene 6 was identified as an HCMV protease inhibitor. Optimization of various regions of the lead molecule using parallel synthesis resulted in 1,6-substituted naphthalenes 19d-i. These compounds displayed good potency and were selective over elastase, trypsin, and chymotrypsin. The optimization approach on lead compound 6 in three different regions of the molecule using parallel solution-phase synthesis and the corresponding SAR are discussed in detail.

  DOI：

  10.1021/jm030540h

文献信息

• <b>Substituent Effects. II.^1a The Preparation of a Series of Substituted 1-Naphthoic Acids</b>
  作者：Michael J. S. Dewar、Patrick J. Grisdale

  DOI：10.1021/ja00877a024

  日期：1962.9
• Adcock,W.; Wells,P.R., Australian Journal of Chemistry, 1965, vol. 18, p. 1351 - 1364
  作者：Adcock,W.、Wells,P.R.

  DOI：——

  日期：——
• Design and Syntheses of 1,6-Naphthalene Derivatives as Selective HCMV Protease Inhibitors
  作者：Ariamala Gopalsamy、Kitae Lim、John W. Ellingboe、Boris Mitsner、Antonia Nikitenko、Janis Upeslacis、Tarek S. Mansour、Matthew W. Olson、Geraldine A. Bebernitz、Diane Grinberg、Boris Feld、Franklin J. Moy、John O'Connell

  DOI：10.1021/jm030540h

  日期：2004.4.1

  Through high throughput screening of various libraries, substituted styryl naphthalene 6 was identified as an HCMV protease inhibitor. Optimization of various regions of the lead molecule using parallel synthesis resulted in 1,6-substituted naphthalenes 19d-i. These compounds displayed good potency and were selective over elastase, trypsin, and chymotrypsin. The optimization approach on lead compound 6 in three different regions of the molecule using parallel solution-phase synthesis and the corresponding SAR are discussed in detail.